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An overview on eco-friendly polyglycerol esters of fatty acid, synthesis and applications 综述了环保型脂肪酸聚甘油酯的研究进展、合成及应用
4区 工程技术 Q4 CHEMISTRY, APPLIED Pub Date : 2023-10-20 DOI: 10.1515/tsd-2023-2509
Suruchi Damle, Chandu Madankar
Abstract Polyglycerol esters (PEGs) which are non-ionic surfactants acting as emulsifiers, wetting agents and viscosity modifying agents are used in the cosmetic, pharmaceutical and food industries. They have been proposed as an alternative to ethoxylated glycol-based non-ionic surfactants due to safety issues. PGEs are composed of fatty acid, which is a lipophilic moiety, and polyglycerol, which is a hydrophilic moiety. They are synthesized by several methods, such as direct esterification of fatty acids and polyglycerols, chemical transesterification of fatty acid methyl esters and polyglycerol, enzymatic transesterification using Lipozyme 435, using glycerol carbonate as raw material, using microwave irradiation, etc. PGEs (Polyglycerol esters) are claimed to be green alternatives to the existing emulsifiers used in the chemical industry as the raw material used for synthesis is obtained from vegetable oils which are renewable, and therefore, eco-friendly surfactants for use in a broad number of applications including food, cosmetics, textiles and personal care. The major challenges in the synthesis of polyglycerol fatty acid esters are to increase yield and control the esterification level while minimising side reactions.
聚甘油酯(peg)是一种非离子表面活性剂,具有乳化剂、润湿剂和粘度调节剂的作用,广泛应用于化妆品、制药和食品工业。由于安全性问题,它们已被提议作为乙氧基化乙二醇基非离子表面活性剂的替代品。PGEs由脂肪酸(亲脂部分)和聚甘油(亲水部分)组成。它们的合成方法有脂肪酸与聚甘油直接酯化法、脂肪酸甲酯与聚甘油化学酯交换法、Lipozyme 435酶促酯交换法、以碳酸甘油为原料、微波辐照法等。聚甘油酯(PGEs)被认为是化学工业中现有乳化剂的绿色替代品,因为用于合成的原料是从可再生的植物油中获得的,因此是一种环保的表面活性剂,广泛应用于食品、化妆品、纺织品和个人护理等领域。合成聚甘油脂肪酸酯的主要挑战是提高收率和控制酯化水平,同时尽量减少副反应。
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引用次数: 0
Transition from a foam-like to an onion-like nanostructure in water-rich L3 phases 在富水L3相中从泡沫状纳米结构过渡到洋葱状纳米结构
4区 工程技术 Q4 CHEMISTRY, APPLIED Pub Date : 2023-10-16 DOI: 10.1515/tsd-2023-2559
Philipp Menold, Reinhard Strey, Stefan Roitsch, Natalie Preisig, Cosima Stubenrauch
Abstract In dilute water-surfactant systems L 3 phases are found in which bilayers interconnect to form a sample-spanning sponge-like structure. From our previous study of the system water/NaCl-AOT (sodium bis(2-ethylhexyl) sulfosuccinate) we know that a transition of this sponge-like structure to an oil-continuous foam-like structure occurs upon addition of minute amounts of oil (about 3 wt%, α = 0.03) in the L 3 channel at a constant surfactant mass fraction of γ = 0.15 and T = 25 °C. The aim of the present study was to verify if the same transition occurs at γ = 0.25. To achieve this goal, we determined the relevant part of the phase diagram and studied the electrical conductivities and viscosities within the narrow one-phase L 3 channel. Although the electrical conductivities and viscosities change qualitatively like those observed at γ = 0.15 we did not observe a sponge-like structure at γ = 0.25 in the oil-free system ( α = 0) with freeze-fracture electron microscopy (FFEM) and freeze fracture direct imaging (FFDI). Together with the FFEM/FFDI images and SANS/SAXS curves we provide experimental evidence for a structural transition with decreasing oil content from a thermodynamically stable foam-like to a thermodynamically stable onion-like nanostructure at γ = 0.25 rather than to a sponge-like structure as is the case at γ = 0.15.
摘要在稀水-表面活性剂体系中,发现了l3相,其中双层相互连接形成跨样品的海绵状结构。从我们之前对水/NaCl-AOT(二(2-乙基己基)琥珀酸钠)体系的研究中我们知道,在表面活性剂质量分数为γ = 0.15和温度为25℃的恒定条件下,在l3通道中加入微量的油(约3 wt%, α = 0.03),这种海绵状结构就会转变为油连续泡沫状结构。本研究的目的是验证在γ = 0.25时是否发生同样的转变。为了实现这一目标,我们确定了相图的相关部分,并研究了狭窄的单相l3通道内的电导率和粘度。尽管电导率和粘度的定性变化与γ = 0.15时相似,但在无油体系(α = 0)中,冷冻断裂电子显微镜(FFEM)和冷冻断裂直接成像(FFDI)并没有观察到γ = 0.25时的海绵状结构。结合FFEM/FFDI图像和SANS/SAXS曲线,我们提供了实验证据,证明在γ = 0.25时,油含量从热力学稳定的泡沫状纳米结构转变为热力学稳定的洋葱状纳米结构,而不是像γ = 0.15时那样转变为海绵状结构。
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引用次数: 0
The use of polyoxyethylene (20) cetyl ether in assessing the hydrophobicity of compounds of biomedical importance and in the process of drug release from microemulsions 聚氧乙烯(20)十六烷基醚在评价生物医学重要化合物疏水性和微乳药物释放过程中的应用
4区 工程技术 Q4 CHEMISTRY, APPLIED Pub Date : 2023-10-05 DOI: 10.1515/tsd-2023-2536
Nino Lominadze, Maya Sebiskveradze, Rusudan Chaladze, Natia Papuashvili, Tinatin Butkhuzi, Maka Alexishvili, Marina Rukhadze
Abstract The creation and study of artificial membranes based on microemulsions is an important direction due to the similarity of the structure of both direct and reverse microemulsions with cell membranes. A microemulsion mobile phase prepared with a non-ionic surfactant in combination with a C18 type stationary phase creates a similar image of the cell membrane in a chromatographic column. In addition, the use of microemulsion systems to transport drugs with low bioavailability into the body can increase their bioavailability. The chromatographic behaviour of model substances of biomedical importance was investigated using micellar mobile phases containing polyoxyethylene (20) cetyl ether in biopartitioning micellar chromatography (BMC) in the concentration range of 1–5 %. Cholic acid was introduced into the polyoxyethylene (20) cetyl ether micellar mobile phase to approximate the structure of the cell membrane. The hydrophobicity of the model compounds was evaluated. Hydrophobicity indices in the micellar mobile phase with and without addition of cholic acid were compared. The release profile of promethazine hydrochloride from microemulsion systems with monomeric and polymeric surfactants was investigated. The kinetic properties of the release of promethazine hydrochloride from microemulsion systems were calculated. It was found that a microemulsion of polyoxyethylene (20) cetyl ether mixed with polyoxyethylene (4) lauryl ether reduced the release of promethazine hydrochloride in weight percent. The release of promethazine hydrochloride from microemulsions does not obey Fick’s diffusion but follows a non-Fick’s transport mechanism, as evidenced by the high values of the diffusion exponent ( n > 0.5).
基于微乳的人工膜的创建和研究是一个重要的方向,因为直接微乳和反向微乳的结构与细胞膜相似。由非离子表面活性剂与C18型固定相结合制备的微乳液流动相在色谱柱中产生类似的细胞膜图像。此外,使用微乳系统将低生物利用度的药物输送到体内可以提高其生物利用度。采用含聚氧乙烯(20)十六烷基醚的胶束流动相,在浓度范围为1 ~ 5%的生物分割胶束色谱(BMC)中,研究了生物医学重要模型物质的色谱行为。将胆酸引入聚氧乙烯(20)十六烷基醚胶束流动相中,以近似细胞膜结构。对模型化合物的疏水性进行了评价。比较了添加和不添加胆酸时胶束流动相的疏水性指数。研究了单体表面活性剂和聚合物表面活性剂微乳液体系中盐酸异丙嗪的释放规律。计算了微乳液体系中盐酸异丙嗪的释放动力学性质。结果表明,聚氧乙烯(20)十六烷基醚与聚氧乙烯(4)十二烷基醚的微乳液可使盐酸异丙嗪的释放量按重量百分比降低。微乳中盐酸异丙嗪的释放不服从菲克扩散,而是遵循非菲克输运机制,扩散指数(n >0.5)。
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引用次数: 0
The interaction of ester functionalized amide gemini surfactants with polymers 酯功能化酰胺gemini表面活性剂与聚合物的相互作用
4区 工程技术 Q4 CHEMISTRY, APPLIED Pub Date : 2023-10-02 DOI: 10.1515/tsd-2023-2515
Yue Lei, Yue Liu, Yuheng Li, Xiaohao Lu, Haiyan Gao, Hujun Xu
Abstract In this study the interaction between the esterified amide gemini surfactant C 12 -(BAE)-C 12 , where BAE stands for the bis(acetoxy)ethane linking group, and the non-ionic polymer polyvinylpyrrolidone (PVP) was investigated by the surface tension method. It was found that there was no apparent interaction between them. The interaction between C 12 -(BAE)-C 12 and sodium polyelectrolyte polyacrylate (NaPAA) was investigated by surface tension, micropolarity and turbidity measurements. The results showed that there was a strong interaction between them. The aggregates were formed by electrostatic attraction between the molecules of C 12 -(BAE)-C 12 and NaPAA in the bulk. This process led to the appearance of two inflection points, the critical aggregation concentration ( cac ) and the critical micelle concentration (CMC), on the surface tension and micropolarity curves. In addition, the inorganic salt NaBr had two opposite effects, promoting or inhibiting the interaction between C 12 -(BAE)-C 12 and NaPAA. This was related to the concentration of NaBr itself.
摘要本研究采用表面张力法研究了酯化酰胺gemini表面活性剂c12 -(BAE)-C 12 (BAE代表双(乙氧基)乙烷连接基)与非离子聚合物聚乙烯吡咯烷酮(PVP)的相互作用。结果发现它们之间没有明显的相互作用。通过表面张力、微极性和浊度测量研究了c12 -(BAE)- c12与聚丙烯酸钠(NaPAA)的相互作用。结果表明,两者之间存在较强的相互作用。聚集体是由c12 -(BAE)- c12和NaPAA分子之间的静电吸引形成的。这一过程导致表面张力和微极性曲线上出现临界聚集浓度(cac)和临界胶束浓度(CMC)两个拐点。此外,无机盐NaBr具有促进或抑制c12 -(BAE)-C 12与NaPAA相互作用的两种相反作用。这与NaBr本身的浓度有关。
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引用次数: 0
Synthesis and surface properties of branched-chain tertiary fatty alcohol sulfate surfactants 支链叔脂肪醇硫酸盐表面活性剂的合成及表面性能
4区 工程技术 Q4 CHEMISTRY, APPLIED Pub Date : 2023-09-28 DOI: 10.1515/tsd-2023-2534
Qian Wang, Xu Li, Jinxiang Dong
Abstract In this paper, anionic branched-chain tertiary fatty alcohol sulfate surfactants were synthesized from n -hexene and n -octene using selective olefin dimerization, hydration reaction (hydroxylation), and sulfur trioxide sulfation. The direct hydration reaction of the α-olefin dimer 2-butyl-1-octene with water as a model reaction was explored for the synthesis of branched-chain tertiary fatty alcohols. Two branched-chain tertiary fatty alcohol sulfate surfactants, namely C 12 -SBTAS and C 16 -SBTAS, with different carbon chain lengths, were synthesized by the sulfur trioxide sulfation method. Their structures were confirmed by various analytical techniques, including HPLC, FT-IR, HR-MS, and 1 H NMR. Equilibrium and dynamic surface tension, foaming, wetting, and emulsifying properties were compared with those of Guerbet cetyl alcohol sulfate (C 16 -SGAS). C 12 -SBTAS and C 16 -SBTAS exhibited good surface activity with equilibrium surface tension ( γ CMC ) values of 27.41 mN m −1 and 26.69 mN m −1 , respectively. They also had low foaming and rapid defoaming abilities, as well as good wetting and emulsifying properties, which match the application characteristics of typical branched-chain surfactants.
摘要以正己烯和正辛烯为原料,经选择性烯烃二聚化、水化反应(羟基化)和三氧化硫磺化反应合成了阴离子支链硫酸叔脂肪醇表面活性剂。以α-烯烃二聚体2-丁基-1-辛烯与水的直接水化反应为模型反应,研究了支链叔脂肪醇的合成。采用三氧化硫磺化法合成了碳链长度不同的支链叔脂肪醇硫酸盐表面活性剂c12 -SBTAS和c16 -SBTAS。通过HPLC、FT-IR、HR-MS和1h NMR等分析技术对其结构进行了确证。比较了古贝十六醇硫酸盐(c16 -SGAS)的平衡和动态表面张力、发泡、润湿和乳化性能。c12 -SBTAS和c16 -SBTAS表现出良好的表面活性,平衡表面张力(γ CMC)值分别为27.41 mN m−1和26.69 mN m−1。具有低发泡和快速消泡能力,良好的润湿和乳化性能,符合典型支链表面活性剂的应用特点。
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引用次数: 0
Wetting behaviour of ionic surfactants on the aluminium foil 离子表面活性剂在铝箔上的润湿行为
4区 工程技术 Q4 CHEMISTRY, APPLIED Pub Date : 2023-09-27 DOI: 10.1515/tsd-2023-2541
Summi Rai, Bishnu Shau Rauniyar, Ajaya Bhattarai
Abstract Aluminium foil is a versatile material used in various industries, but its inherent low wettability limits its application. Surfactant can be used as effective agents for enhancing the wettability, enabling improved surface interactions and performance. In this study, we investigated the wettability of anionic (SDS and AOT) and cationic (CTAB) surfactants prepared in water as well as in isopropanol-water solvents with the four different volume fractions (0.1, 0.2, 0.3 and 0.4) on aluminium foil surfaces by measuring the contact angle. As the volume fraction of isopropanol on aluminium foil increases, the contact angle of SDS, CTAB, and AOT increases whereas the surface free energy decreases, indicating the hydrophobic nature of the surface. This trend is observed with the increasing concentrations of various solvents used. The adhesion work exhibits a linear increase with alcohol surface tension. A curvilinear variation is observed in the plots between cos θ $theta $ and 1/ γ SL $sqrt{{gamma }_{text{SL}}}$ . The plots of adhesion work versus contact angles show non-linear variation. Additionally, the plot of cos θ $theta $ against the surface tension of alcohol and adhesion work against log C exhibit curvilinear variation. With these results, the article aims to provide valuable insights into the application of surfactants for improving the wettability of aluminium foil.
铝箔是一种用途广泛的材料,应用于各个行业,但其固有的低润湿性限制了其应用。表面活性剂可以作为增强润湿性的有效剂,改善表面相互作用和性能。本研究通过测量接触角,考察了制备的阴离子(SDS和AOT)和阳离子(CTAB)表面活性剂在水和异丙醇-水溶剂中(体积分数分别为0.1、0.2、0.3和0.4)对铝箔表面的润湿性。随着异丙醇在铝箔上的体积分数的增加,SDS、CTAB和AOT的接触角增大,而表面自由能减小,表明表面具有疏水性。随着所用各种溶剂浓度的增加,可以观察到这种趋势。附着力随乙醇表面张力呈线性增加。在cos θ $theta $和1/ γ SL $sqrt{{gamma }_{text{SL}}}$之间的图中观察到曲线变化。黏附功随接触角的变化曲线呈非线性变化。此外,cos θ $theta $对乙醇表面张力和黏附功对log C的变化曲线。根据这些结果,本文旨在为表面活性剂在改善铝箔润湿性方面的应用提供有价值的见解。
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引用次数: 0
Influence of surfactant concentration on selected quality parameters of fruit washing agents 表面活性剂浓度对水果清洗剂质量参数选择的影响
4区 工程技术 Q4 CHEMISTRY, APPLIED Pub Date : 2023-09-20 DOI: 10.1515/tsd-2023-2543
Zofia Hordyjewicz-Baran, Tomasz Wasilewski, Magdalena Zarębska, Artur Seweryn
Abstract In this study, special types of washing agents, intended for fruit washing were developed. Fruit washing agents with different contents of non-ionic surfactants have been prepared. The developed products were characterized in terms of performance with regard to their ability to remove pesticide residues from fruit surfaces. Special attention was paid to the safety of use in relation to the level of skin irritation during washing. The results provided important information on the effect of surfactant concentration on selected quality parameters of the developed fruit washing agents.
摘要:本研究开发了专用于水果洗涤的清洗剂。制备了不同含量的非离子表面活性剂的水果清洗剂。开发的产品在性能方面具有去除水果表面农药残留的能力。特别注意的是,在清洗过程中,与皮肤刺激水平有关的使用安全性。研究结果为表面活性剂浓度对果蔬清洗剂品质参数的影响提供了重要依据。
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引用次数: 0
Preparation, characterization, and stability of lipid nanoparticles including unsaturated lipids 脂质纳米颗粒的制备、表征和稳定性,包括不饱和脂质
4区 工程技术 Q4 CHEMISTRY, APPLIED Pub Date : 2023-09-20 DOI: 10.1515/tsd-2023-2544
Yeseul Park, Jin-Won Park
Abstract Among the SARS-CoV-2 vaccines developed to date, the mRNA vaccines developed by the Pfizer/BioNTech and Moderna companies have been formulated using saturated lipids, specifically 1,2-distearoyl- sn -glycero-3-phosphocholine (DSPC), along with cholesterol. DSPC and cholesterol have the disadvantage of causing sclerosis. Therefore, in this study, lipid nanoparticles (LNPs) were prepared and characterized by replacing DSPC with 1,2-dioleoyl- sn -glycero-3-phosphocholine (DOPC) and excluding cholesterol. The results showed that the DOPC-based LNPs had a smaller diameter (75.67 nm) compared to the previous study and the polydispersity index (PI) indicated a good dispersion homogeneity, suggesting size uniformity. Additionally, the LNPs maintained their size between 57 nm and 152 nm and showed stable PI values (0.330–0.393) throughout the 25 days.
在迄今为止开发的SARS-CoV-2疫苗中,由辉瑞/BioNTech和Moderna公司开发的mRNA疫苗使用饱和脂质(特别是1,2-二硬脂酰- sn -甘油-3-磷酸胆碱(dsc))和胆固醇配制。DSPC和胆固醇有引起硬化症的缺点。因此,本研究制备了脂质纳米颗粒(LNPs),并用1,2-二油基- sn -甘油-3-磷酸胆碱(DOPC)取代dsc并排除胆固醇,对LNPs进行了表征。结果表明,dopc基LNPs的直径(75.67 nm)比之前的研究要小,多分散性指数(PI)显示出良好的分散均匀性,表明尺寸均匀。在25 d内,LNPs的尺寸保持在57 ~ 152 nm之间,PI值稳定在0.330 ~ 0.393。
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引用次数: 0
Simulation of adsorption at rotating disk 旋转圆盘吸附的模拟
4区 工程技术 Q4 CHEMISTRY, APPLIED Pub Date : 2023-09-12 DOI: 10.1515/tsd-2023-2522
Milivoj Lovrić
Abstract Diffusion-controlled adsorption at the rotating disk is calculated for Frumkin isotherm. The near equilibrium isotherms are simulated and their time components are analysed. The purpose of the work is to investigate the physical meanings of S-shaped isotherms that appear for strong attractions in the adsorbed layer. It is demonstrated that the surface coverage that is created gradually, by the diffusion process, consumes the concentration gradient of the dissolved surfactant in the diffusion layer. Once the equilibrium with the bulk of the solution is established, the driving force of diffusion-controlled adsorption vanishes and no additional adsorption is possible. The diffusion layer thickness on the rotating disk tends to the constant value and the flux depends only on the concentration of dissolved adsorbent at the disk surface. Hence, the equilibrium with the bulk of solution is established faster than at the stationary disk. This equilibrium takes an infinite amount of time to reach, but the system can approach close to the equilibrium within a definite period of time. The near equilibration time depends on the bulk concentration of surfactant. These relationships exhibit sharp maxima under the influence of attractions in the adsorbed layer.
摘要采用弗鲁姆金等温线计算了旋转盘上的扩散控制吸附。模拟了近平衡等温线,并对其时间分量进行了分析。这项工作的目的是研究在吸附层中出现的强吸引力的s形等温线的物理意义。结果表明,扩散过程逐渐形成的表面覆盖消耗了扩散层中溶解表面活性剂的浓度梯度。一旦与大部分溶液建立平衡,扩散控制吸附的驱动力就消失了,并且不可能再进行吸附。旋转圆盘上的扩散层厚度趋于恒定值,通量仅取决于圆盘表面溶解吸附剂的浓度。因此,与大部分溶液的平衡比在固定圆盘上建立得更快。这种平衡需要无限长的时间才能达到,但系统可以在一定的时间内接近平衡。接近平衡时间取决于表面活性剂的体积浓度。这些关系在吸附层中的吸引力影响下表现出明显的最大值。
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引用次数: 0
Influence of tetrabutylammonium bromide based ionic liquid on the aggregation behavior of dodecyltrimethylammonium bromide in the range (293.15 K–313.15 K): acoustic and volumetric investigation 四丁基溴化铵离子液体对十二烷基三甲基溴化铵在(293.15 K - 313.15 K)范围内聚集行为的影响:声学和体积学研究
IF 1 4区 工程技术 Q4 CHEMISTRY, APPLIED Pub Date : 2023-09-01 DOI: 10.1515/tsd-2023-2523
H. Hooshyar, Rahmat Sadeghi
Abstract The effect of the ionic liquid analogue tetrabutylammonium bromide on the aggregation behaviour of the cationic surfactant dodecyltrimethylammonium bromide in aqueous medium was investigated with volumetric and compressibility measurements over a wide temperature range (293.15–313.15) K. The data obtained were used to obtain density data. Based on the density data obtained, the volumetric properties (apparent molar volumes and partial molar volumes) of the surfactant in unimeric and micellar forms were evaluated and discussed in terms of the respective ionic and dipolar interactions. The data obtained were analysed to determine the effects of (i) temperature and (ii) salt added to the surfactant. The results were also interpreted in terms of the molecular interactions occurring in the binary mixtures of the present study. The addition of tetrabutylammonium bromide has a lowering effect on the CMC values of the surfactant studied in aqueous medium.
研究了离子液体类似物四丁基溴化铵对阳离子表面活性剂十二烷基三甲基溴化铵在水介质中聚集行为的影响,并在宽温度范围(293.15 ~ 313.15 k)内进行了体积和可压缩性测量。根据所获得的密度数据,从离子和偶极相互作用的角度评估和讨论了表面活性剂在单聚体和胶束形式下的体积性质(表观摩尔体积和偏摩尔体积)。对得到的数据进行了分析,以确定(i)温度和(ii)表面活性剂中添加的盐的影响。结果也解释了分子的相互作用,发生在二元混合物的本研究。四丁基溴化铵的加入对表面活性剂的CMC值有降低作用。
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引用次数: 0
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Tenside Surfactants Detergents
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